Diisopropylamine → 5-(4-Butoxyphenylethynyl)furan-2-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]amide

HRID 1354733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354733
[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[O:18][C:19](Br)=[CH:20][CH:21]=3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1.[CH2:24]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]#[CH:36])=[CH:31][CH:30]=1)[CH2:25][CH2:26][CH3:27].C(NC(C)C)(C)C>CN(C)C=O.O1CCCC1.[Cu]I>[CH3:1][N:2]([CH3:23])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[O:18][C:19]([C:36]#[C:35][C:32]4[CH:33]=[CH:34][C:29]([O:28][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:30][CH:31]=4)=[CH:20][CH:21]=3)=[O:16])=[CH:10][CH:9]=2)[CH2:4]1

Komponenten

7

Edukt 3

HCID 7912DiisopropylamineHCID 27751201-Butoxy-4-ethynylbenzeneHCID 671477595-Bromofuran-2-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

Produkt 1

HCID 588665915-(4-Butoxyphenylethynyl)furan-2-carboxylic Acid [4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Bromofuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide (75 mg) was dissolved together with 1-butoxy-4-ethynylbenzene (35 mg) in N,N-dimethylformamide (1 ml) and, under argon, added dropwise to a suspension of Pd(tBu3P)2Cl2 (4 mg), copper (I) iodide (75 mg) and N,N-diisopropylamine (20 mg) in anhydrous tetrahydrofuran (3 ml). The mixture was stirred at room temperature for 8 hours. The reaction was worked up by filtration through a syringe filter and concentrated, and the crude product was purified by preparative HPLC. This resulted in the product with the molecular weight of 471.6 (C29H33N3O3); MS (ESI): 472 (M+H+) as hydrotrifluoroacetate.

Aufarbeitung

  1. filtrationThe reaction was worked up by filtration through a syringe
  2. filtrationfilter
  3. concentrationconcentrated
  4. customthe crude product was purified by preparative HPLC
  5. customThis resulted in the product with the molecular weight of 471.6 (C29H33N3O3)

Quellen und Nachweise

ORD-Eintrag
ord-0883b1b3017d4a72b091ab30ed93b649
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223788B2

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